


Deal Me In

by kasey1939



Series: Deal [1]
Category: Supernatural
Genre: Castiel is more than he appears, Deal AU, Fallen Cas, M/M, Plot Twists, Possessive Cas
Language: English
Status: In-Progress
Published: 2015-06-18
Updated: 2016-05-10
Packaged: 2018-04-05 01:36:48
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 10,194
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4160679
Author URL: https://archiveofourown.org/users/kasey1939/pseuds/kasey1939
Summary: <blockquote class="userstuff">
              <p>When Dean goes to the cross-roads to save his brother he thinks he knows what's going to happen until his deal is hijacked by someone a little strange who doesn't seem to be following the rules.</p>
            </blockquote>





	1. Lets Make a Deal

**Author's Note:**

> [](http://s1063.photobucket.com/user/kasey19391/media/Done%20Story%20Banners/Deal%20me%20in%20.jpg.html)
> 
>   
>    
> 

**Summary for the Chapter:**

> Dean goes to make his deal to save Sam and gets a surprise visit at the crossroads.

**Notes for the Chapter:**

> Disclaimer – 1 amazing show + 1 hopefully at least half as good idea = owning nothing to do with the amazing show and everything to do with the hopeful idea. I earn nothing, make nothing (besides this little ditty), so trying to sue me would net you a whole load of nothing.

[](http://s1063.photobucket.com/user/kasey19391/media/Chapter%20art/Deal%20me%20in/Chapter%201.jpg.html)

  
  


Castiel remembered the first time he saw Dean Winchester. He’d known who he was to become and his curiosity mounted until he sought him out.

The boy had been ten years old, holding a shotgun, watching over his younger brother with such a fierce look of determination on his face, such love and loyalty that he had fallen in love then and there. Of course Dean would not know of his existence until years later when their relationship would truly begin.

Their romance did not start with a passing glance or a chance meeting as most do, no, the saga of Castiel and Dean truly began with the death of Sam Winchester and a deserted crossroads.

Dean stood out in the cold fighting both his tears and his instincts. Sammy was dead and he had to do something! This, was the only option left to him, he knew a demon would deal, they just loved taking Winchesters.

As he finished smoothing out the dirt he stood and waited.

“Hello, Dean, what brings you by?” He turned to face the woman he would have thought beautiful had he met her anywhere else for any other reason.

“Bring Sam back.” He didn’t have time for stupid demon small talk.

“Now why would I do that?” He knew what she wanted him to say, so he swallowed his pride for Sammy, and said it.

“For my soul.” He saw her eyes brighten like she was hoping he would say that, like he’d be here for any other reason.

“Oh, here to make a deal then? Fine, I’ll bring baby brother back and in one year you go downstairs to meet everyone.” He tried to keep his face blank but his shock must have showed.

“What did you think we’d give you ten years to keep hunting us? Oh, no sweetness, you Winchesters are too much of a nuisance to wait that long, but hey if you don’t want it I’m sure you’ll adjust just fine to being all alone. You Winchesters are resilient after all.” He didn’t even hesitate. He couldn't.

“Deal.” It was his job to keep Sam safe, how could he do anything else.

“Good boy, now come on handsome don’t be shy, give us a kiss.” He leaned in, but just as their lips were about to touch she was slammed back from him with such force she landed ten feet away. In her place stood a … IRS Agent?

“Sorry, this is above your pay grade.” Dean was slightly shocked that such a deep voice came from such a small guy. The man walked towards the fallen demon and just as Dean regained enough of his brain cells to ask What the Hell he laid his hand on her shoulder and lit her up like a jack-o-lantern.

Um, that was new, he'd been hunting shit for nearly his whole life but he'd never even heard of something being able to turn a demon into a lite-brite. He instinctively looked around for a way out, but then he thought about Sammy, he couldn’t leave yet he still had a deal to make.

As the man turned to him, the demon dead at his feet, Dean gathered all his courage and looked him dead in the eye, which seemed to amuse him. Great.

Castiel did not even try to keep the smile from his face when he saw the light of determination enter Dean’s emerald eyes. When he had heard the deal Dean was making he could not stand it, Dean was his! He had permission from his brother, Lucifer, the time differences between hell and earth were really useful at times, and the hunter would be his so long as he still broke the first seal.

He hated the idea of breaking Dean, mostly, but he would lovingly put him back together once his role was done. First things first.

“Do you still wish to make a deal?” He knew he would, he would have already tried to either attack or escape if he didn't still wish to make his deal.

“You can do that? I mean you got the juice to bring Sam back?” He would be offended at the lack of faith in his abilities, but he had to remind himself that Dean did not know as much about him as he did about his beloved. This vessel did not exactly scream power, so the question was valid in a way.

“I can do what you’re asking and in one year your contract shall be fulfilled. Do we have a deal?”

“Yes!” Dean answered in a rush as though he thought Castiel would change his mind. Or maybe it was not Castiel’s mind he feared would be changed with time. Interesting.

“It is a deal then.”

Castiel watched as Dean took a step closer to him closing the distance between their bodies. He had been waiting to know the taste of Dean’s lips for years and now the wait would be over. The kiss when it came was not nearly long enough, but he contented himself with the knowledge that it would simply be the first of many. He only needed to wait one more year and Dean would finally be where he belonged. At his side.

Dean pulled away trying, and thanks to years of practice succeeding, to ignore the spark he felt when their lips met.

“Sammy?”

“I will go now to fulfill my end of our bargain. He will be alive and well by the time you arrive back at his side. Oh, and one more thing.” Without warning the demon reached up and grasped his shoulder tightly and he felt the most blinding pain he’d ever felt in his life. The only times that even came close to this sensation was when he’d been so close to death it was a miracle he was standing here now.

By the time the pain subsided Dean looked up from his place on the ground to find he was alone. The prick had left, to heal Sammy, that thought got him moving like nothing else ever would or could. He needed to get to Sam, see for himself that he was alright, and see with his own eyes that this deal was worth it.

Castiel looked down at the corpse of Sam Winchester and felt… nothing. This boy, like his brother, had a role to play in the coming days, but Castiel felt nothing for the one who would one day become his brothers’ vessel on earth. Reaching down to touch his head he sent his grace out seeking his soul, he would restore Samuel Winchester to just as he had been before his death. He had to be perfect, he would be his first gift to Dean after all.

He woke with a gasp looking around wildly to gain his bearings. Castiel saw him tense the moment he realized he was not alone in the room. The Winchesters were truly remarkable, not even death dulled their instincts.

“Hello, Sam.”

“Who are you?” The question came out as more of a demand, which made him frown at the disrespect. He decided to let it pass, the boy had been through a lot and he did owe him for finally being one step closer to Dean.

“I am the one your brother sold his soul to in exchange for your life.” His use for the younger Winchester over for me moment, he flew back towards his brother to thank him for his generosity. Dean Winchester would finally be his.

Sam stood alone in the run down shack he woke in trying to calm his frantic mind. Dean sold his soul for him? No, he couldn't, he wouldn't would he? Who was he kidding of course he would do something like that, this was Dean he was talking about. The question wasn't what Dean had done, thinking of the past would get them nowhere, it was over and done, now he needed to focus on what came next.

The man, creature, who'd been there when he woke had left before he could get his head on straight enough to demand details, which he supposed was a good thing his demand to know who he was had seemed to annoy the thing, and annoying something with the juice to do a deal like this probably wasn't the best idea in the world.

When he heard the Impala pull up he ran his hands through his hair and told himself again that he wasn't going to yell at his brother. That raised voices wouldn't get them anywhere, that to get anything out of Dean he had to remain calm. Of course when the door opened and his brother stepped inside all that went right out the   
window as usual.

"What the hell did you do Dean?"

"What do you mean what did I do?" Dean was using his admit to nothing tone.

"Cut the crap, the guy you made the deal with was still here when I came to, he told me about your deal to save me."

"If you already know then why you asking?"

"Because I wasn't really asking what you did, I was asking how you could be so stupid to trade your life for mine."

"You're my brother Sammy."

Closing his eyes he counted to ten. There it was all laid out in the open the reason Dean did anything. Family was everything to Dean and he would die to protect anyone he considered family, blood or no. For Sam he would do a lot worse than die apparently.

"Yeah, Dean, I'm your brother. You're my brother to Dean, and I'm telling you now I won't let you go to hell. Not for me."


	2. Across a Smokey Room

**Summary for the Chapter:**

> Dean's just trying to relax but he finds something unexpected at a bar.

[](http://s1063.photobucket.com/user/kasey19391/media/Chapter%20art/Deal%20me%20in/Chapter%202.jpg.html)

  
  


It had been two weeks since Dean had made his deal and Castiel was on fire with anticipation. Time had never moved so slowly in his entire existence, he couldn't seem to stay away from Dean for more than a few hours which in its self was torture. Sweet torture but torture none the less.

He watched as the boys returned to Bobby Singer, their surrogate father, and he continued to watch as the older man berated his beloved for making his deal. It had taken all his will not to intervene and smite the foolish mortal for his thoughtless words, but he knew that Dean would never forgive such a thing, this man was family to Dean and to Dean family was everything.

Now after thirteen days he watched as the newly resurrected Sam Winchester continued to look for a way to release Dean from his deal. He would be furious about this if he had thought for a second that the boy would succeed. He knew there was no chance of that however so he chose to look on the situation with amusement instead. 

He had watched as day after day Sam and Bobby got more absorbed in their research and he watched as day after day Dean chafed more and more at his confinement at the Singer Salvage Yard. Until finally he snapped.

"Look I got a limited number of days left and I ain't spending any more of 'em here staring at walls and watching old reruns. Sammy you can either get your big head out of those books and come with me on a hunt or I'm going solo. I swear I will."

He would to, he had seen that look of determination on his future lovers face before, and he meant every word he said.

"Dean we're trying to save you will you please just be patient for once in your life." Sam sounded more impatient than he believed he should. He should know his brother well enough to have seen this coming.

"Hey! I've been patient for two whole weeks, that's like a record for me, now I'm going stir crazy. So I'm leaving either come with me or don't." Without another word Dean left to pack his things.

"Damn it! You'd think he'd be at least a little more interested in saving his own life." Sam dropped is head in his hands, his irritation getting the better of him.

"Well now, you know your brother Sam he needs to keep busy when he's facing things like this, it's how he copes with bad situations." Bobby seemed to be nodding along with his own assessment as he continued to flip through the book in front of him. For him Deans behavior seemed to be no surprise at all.

"You mean by not coping at all. He can't just ignore this Bobby; it's not going away on its own." Sam pushed away from the table to pace behind his chair, his displeasure surrounding him like a miasma. 

"I know that you idgit and deep down so does your bone headed brother. Look we got time, so why don't you two hit the road and I'll keep trying to make heads or tails of things here."

"No! We need to keep going; we need to find a way to save him." With that said Sam slammed his body back into his chair and forcefully pulled another book towards him determined to continue with his research.

"We can't exactly let him go off on his own right now, with where his heads at he's like to get himself killed before we can save his life."

"I guess you're right."

"Of course I am, now go on now and leave an old man in peace to read about demonic deals."

Castiel watched as Sam ambled upstairs to prepare to leave before moving to look over the other man's shoulder to see what he was reading. As far as he knew there were no texts about demonic deals on Earth.

Hmmm, it would seem the old man was full of surprises. He had somehow managed to gain one of the few books about such deals, unfortunately for him it was written in a dead language he seemed to be having trouble translating, although he was making good progress, not that it would help him in the end.

The book he had was about how crossroad deals were made and even about how to break them as he wanted, however the only way to break a deal was for the one who made it to break the contract. He had no intention of ever doing that, Dean was finally his he only needed to wait a short time longer, and nothing would ever move him to change that fact.

Dean sat in the Impala trying to keep calm but every mile away from Bobby's made that harder. His brother just would not let up about how stupid he was to leave now when they were so close to finding a way to save him.

They just didn't understand! He knew deep down that there was no saving him. There had just been something about that creature who'd taken over his deal, he couldn't quite place it, but there was just something off about him.

He'd met more than a few crossroads demons in his day of all shapes and power levels but nothing like that guy. The power coming off of him especially when he'd grabbed his shoulder had been unlike anything he'd ever seen before. Not even the demon that’d killed his parents had come close to it and that had been one bad dude.

Resisting the urge to reach up and rub the new hand shaped scar on his shoulder he tried to piece it all together. He was missing something, he knew that much, he just couldn't seem to see the whole picture no matter how hard he tried. Shaking his head he decided to focus on something else, what he needed was a good old fashioned straight forward hunt.

Castiel had watched Dean for years and as a result knew just about everything there was to know about him. Yet, every day he found something new and fascinating to focus on a new layer that just added to the mystery that was his beloved mate. Dean was his he had no doubt of that, and he would not allow Dean to doubt it either when the time came, but for the moment that was his secret to keep.

For the moment Dean thought himself independent and free to do as he pleased, he thought that until the deal came due he would not see Castiel again, that for a year he would be able to just do whatever he wished. He knew he would have to correct this assumption soon, before Dean did something he would later come to regret.

Watching Dean in a bar was an education, everyone male and female alike would stop and take notice of him as he walked by, but he found that their lustful thoughts bothered him now more than they ever had in the past.

He knew Dean was no saint and if he was being honest he liked him far better as a sinner than he would as anything else. He had watched him with others over the years enjoying the sins of the flesh and knew that his future lover was very skilled in this area. Dean had never been with a man before, which is why he chose this vessel in the first place it would have been just as easy to find a female, he wanted to be Dean's first in some way.

He watched as a woman at the bar in a low cut top and short skirt zeroed in on Dean as her intended bedmate for the night, and felt rage begin to boil in his blood. How dare she look at what was his with such hunger, Dean was his not hers, he would not allow her to lay hands on his future lover.

With that thought came another; he did not want any hands but his own touching Dean. He knew it would now be less than a year before he finally owned his precious little one in all ways but that just was not enough.

He needed to make things clear to Dean, and more importantly to the floosy that was currently rubbing her hands up and down his chest. Dean belonged to him and with him, no one else.

Dean sat at the bar waiting for Sammy to finish checking them into the hotel across the street, he figured he deserved a few beers after his last few days. He had sold his soul to save his brother’s life and now his brother had decided that meant he was no longer allowed to make any decisions without a second opinion.

Apparently loving his brother meant he was no longer of sound freaking mind!

His little brother was a mother hen at the best of times always telling him to obey the law and mind his manners like he was some chick. Now, he had taken it to a whole new level treating him like an escaped psych patient or something! Well, he had a cure for that, the moment he walked in the place he'd clocked the hot honey at the bar and as luck would have it the feeling was mutual. Now he would just seal the deal and take her back to HIS room where they would have sex on HIS bed and HIS brother could just get the fuck over it if he didn't like it.

He was about to propose just that to Marlene, Mary, Maggie whatever when he suddenly saw the demon who made his deal smirking behind her. He knew from the look on his face that he was planning something horrible.

"Listen, sorry sweetness but I need you to take a hike a friend of mine just arrived."

"Girlfriend?" That seemed to amuse the demon even more.

"Worse, but I just need you to go." He gave her his best no hard feelings smile and lightly shoved her on her way.

"What the hell are you doing here? I shouldn't be seeing you for eleven and a half months so shoo fly stop bothering me." He knew this thing was powerful enough that he should be at least pretending to show it respect, but that just really wasn't his style. He spoke his mind all his life and nothing and no one would ever change that, least of all the thing that was going to end his life

"What made you think you would not be seeing me exactly? The deal you made was not of the norm so why would the following time be?"

Good point he supposed not that he was feeling very charitable but he needed to know what he was doing here.

"Point to you I guess, now what the hell are you doing here? You're not about to get all mass murder-y on all these people are you?" He glanced around the crowded bar, mentally counting up the body count that would cause.

"And if I said yes what would you do?"

That brought him up short he had no idea. He didn't know any strengths or weaknesses hell he didn't even know what he was, not really, he knew demon but not what kind. If he decided to start slaughtering people then he and everyone else in here were screwed.

"Why are you here?"

It looked for a moment like he wasn't going to let it go. Like he might insist on an answer but then he let it go making him take a deep breath in relief. If he had pressed it he had no idea what his answer would have been and if he'd learned anything about the supernatural that was no way to start a fight.

"I am here to see you Dean. You have a case and I wish to give you my assistance."

"Why?" He might be different, but he was still an evil SOB, and that meant that being helpful just didn't go with the territory.

"Because I find hunters fascinating. You are all such strange creatures most of you are so unlike the other humans who occupy this planet. I wish to observe a hunt up close and now I have my very own hunter, so I thought why not?"

That didn't sound so bad he guessed, it wasn't like he was going to show up on every hunt he just wanted to see one and if it meant he was occupied and not killing everyone in the bar he supposed he could let it slide.

Just this once though, being around the dude who now owned his soul was just plain weird.

"Fine." Tossing some money on the table to pay for his beer he got up and headed for the door to meet Sam outside and tell him the good news. They were now a demons version of the Discovery Channel.

Castiel watched him walk away and felt his head tilting slightly of its own accord as he watched him go. Damn he loved that body, and soon enough it would be all his, until then he would spend time with Dean when he actually knew he was there, he was thrilled.

He knew Dean was assuming that he would only be coming along on this one hunt and then he would leave him alone until his deal came due, he really needed to work on that with his hunter. He left far too much to assumption, his deal now this, he always just assumed he knew the terms.

He would do nothing about it for the moment because it was aiding him in getting what he wanted but soon enough he would point out the error of his ways and teach him a new way, his way.

Sam knew something was wrong the moment he spotted his brother walking towards him from across the parking lot. Towards him and away from the bar. He had just opened his mouth to ask what had happened when he saw the man following close behind Dean, the demon who had sealed his brother’s deal. 

What the hell!

He was close to blasting the guy with exactly what he thought of him but one look from his brother kept him silent. Something was definitely wrong and he supposed he would just have to wait to find out what, talking in front of the demon didn't seem to be an option at the moment.


	3. A New Deal

**Summary for the Chapter:**

> Having Castiel around wouldn't be so bad if Sam would just stop talking.

[](http://s1063.photobucket.com/user/kasey19391/media/Chapter%20art/Deal%20me%20in/Chapter%203.jpg.html)

  
  


A Seer that's what was causing all of this? Dean was having a little trouble wrapping his mind around that one. How could being able to see the future translate into all this pain and chaos?

Who was he kidding? He could see how this whole mess got started he just wanted to stall to try and stay out of the hotel room and away from the demon waiting there for as long as possible. He didn't know what it was about this _Castiel_ but the way he looked at him made his skin crawl, it was possessive, almost obsessive. He knew his brother had noticed, he'd been on the receiving end of his baby brothers bitch face too often to not be able to recognize it when it was directed at others. His brother wasn't the one he was worried about, it was the demon.

He didn't know enough about him to gauge his reaction to Sam's very obvious dislike. If soul boy decided to take exception to one of his brothers none too subtle little digs there wasn't one damn thing he'd be able to do about it and he didn't trade his soul for Sammy's life just to have him throw it away with some dumb ass comment aimed at the guy who'd resurrected him in the first place. That would just be beyond stupid.

Taking a deep breathe to steady himself he pasted on his trade mark look of impatient boredom and opened the door to world war three.

Castiel was beyond done with the younger Winchester and his comments about himself and Dean. The little jibes about him he could take, he cared not what the little insignificant worm thought of him, his destiny and purpose in life was to be vessel for his brother Lucifer no more.

However, all the attacks against Dean and subtle cracks about his mates seeming lack of intelligence was grating to the extreme. He knew everything about Dean and how he portrayed to others that he was far less intelligent than he was, that did not excuse the remarks of his brother. His flesh and blood should be able to see past the mask of ignorance and dull wit to the man beneath.

While it was true that Dean lacked the patience for research that did not make him unknowledgeable about the creatures he grew up hunting. What he lacked in research he more than made up for with instinct and creativity.

“If you are wise Winchester you will cease your incessant litany of insults at once.”

“Oh, I’m sorry did I hurt your little demonic feelings?” He thought he was speaking of the unimaginative comments aimed at him. The boy was truly slow if he thought that.

“No, though I find the sound of your voice most irritating.” He kept his voice level, not giving voice to his true anger, while his eyes drifted around the room never staying on the younger man for longer than a moment.

“Well if you don’t like it so much why don’t you go somewhere else? Don’t you have some other dumb shmuck’s soul to steal?” Did he truly see his brothers sacrifice this way, as though he had been too stupid to see the consequences?

As if he would ever leave his precious Dean alone with his “loving” brother. As Sam had hurled out his insults while watching him for even a twitch of reaction he had been watching Dean and with every slur he watched his mates precious mask chip away even more. With every mention of his deal and the idiocy of it he would retreat farther and farther into himself until he could take it no longer and under the guise of boredom he had escaped in search of food.

“Or I could simply kill you. My deal with your brother was that I would bring you back to life, it does not affect my deal with him at all if you were to die again. You would be dead and I would still get your brother, I see that as a win-win for me. How about you?”

Finally the fool was speechless, maybe instead of killing him he would simply render him mute.

“You son of a bitch!”

Just as Sam stood in aggression the door opened and Dean entered. His attention was immediately focused on Dean and nothing else; Sam had no hope of hurting him after all.

Watching the emotions playing across his lover’s face he was once again struck with just how passionate and deep Dean’s emotions were. Seeing horror fill his features he looked over towards Sam to find the cause just as the knife plunged deep into his chest breaking bone and imbedding its self in his vessel’s heart. Looking up he saw Sam’s face filled with malicious glee and triumph.

Looking down he saw the handle of Ruby’s demon killing blade and understood his attackers look of victory, however misplaced it may be. Slowly he grasped the handle and pulled the blade free without flinching; looking up right into the eyes of Sam Winchester he released it letting the knife fall harmless and useless onto the floor. Smirking he watched the panic set in and he spoke of Dean’s foolishness and rash choices, now what?

Dean could not believe it, any of it. Not only had his brother been stupid enough to attack Castiel in the first place, but he botched it. Now they had one seriously pissed off demon on their hands and one they had no idea how to hurt let alone kill. If the demon killing blade didn't even make him flinch it wasn't like they had a lot of other options, and right now their options were limited to none at all.

The look on Castiel’s face was clear enough for even him to understand. He was amused by what Sam had done. Watching the demon stand he knew he wasn’t about to just let it go, he was going to retaliate against Sammy, he couldn’t let that happen. This thing was beyond powerful, there was no telling what he could do to Sam. Stepping forward he placed himself between Sam and Castiel, causing the demon to pause and tilt its head slightly as if confused.

Reaching behind him he grabbed Sam, without once breaking eye contact with the demon in front of him, he shoved his brother as best he could from the awkward angle towards the door.

“Dean?”

“Get out of here Sammy.”

His tone left no room for argument, as he heard the door close the demon did exactly as he hoped. He looked back and forth from the door to Dean as though conflicted over his options, now he just hoped that the demon’s obsessive staring was real enough that he would choose to stay alone with Dean when given the choice and not go after Sam.

Castiel was torn. The need to make Sam Winchester suffer for his behavior was overwhelming but the chance to spend time alone with Dean was too good to pass up. Looking at his beloved he saw the panic and dread that filled his eyes and knew what Dean was doing. He was once more trading a piece of himself for his brother’s well-being. Hopefully one day before he became his brothers vessel Sam would come to realize just how much his brother always sacrificed for him.

Deciding to see what would happen he slowly sank back down into his chair and watched the relief flood his eyes. He could always harm Sam later but he didn’t think that pointing that out would be very productive.

“Your brother has injured me; he has tried to kill me.” Stating the facts of the situation seemed as good a place to begin as any other.

“Yeah, but he didn’t.” Dean remained stubborn, his eyes never wavering from his own. He found he enjoyed it.

“His failure to reach his goal does not excuse him from retribution.”

“Okay what do you want?” Interesting.

“Why do you think I want anything?”

“Because if there was nothing I could do to stop you from tearing into Sam you wouldn’t still be here, you’d have gone after him already. So what do you want?” True enough, if a little short sighted, his darling boy was learning. Slowly.

“How would you like to make another deal?”

Dean felt his insides turn to ice at the question. He knew he wouldn’t like this when the demon had sat down but even the thought of making another deal filled him with real honest to god fear. But he knew that if he didn’t then Sam would die and he didn’t go through all of this just to lose Sammy now, so really there was only one answer to give.

“What did you have in mind?” What else was there to give?

Castiel was beyond elated by his mate's words, he knew just what he wanted to ask for, now all that was left to do was to make so that Dean had no other option but to surrender to his demands.

"Ten dates."

He watched the confusion overshadow his other emotions while he tried to understand what was happening. Of all the different scenarios he'd watched play across his mind in his expressive eyes he doubted this had been among them. Now the gap between expectation and reality was too large for him to cross swiftly so he simply waited patiently for his slower human mind to catch up.

"What?"

"The deal I am willing to make is in exchange for me taking no lethal or physically harmful action against your brother for his actions this night you will agree to go on ten dates with me." Of course this deal would not stop him from psychologically harming the younger Winchester but he would not point that out. It would also not prevent him from taking action against him in future, for he was certain that the younger man had far from learned his lesson.

"Why? What could you possibly get out of that?" He saw it written all over his mates face. Confusion over the terms, suspicion that he was missing something, fear that this would not work and his brothers heart would once again cease to beat.

"That is none of your concern, you have only one thing to do here, and that is to make a decision. Yes or no. What is your answer?"

"What kind of dates?"

"I have yet to decide." He had so many ideas it was hard to choose just ten, so he supposed he would decide as they went along.

"So basically what you're sayin' is that either I agree to go on ten unspecified dates with you at some point between now and the end of my deal or you kill Sammy right now?"

"You have summarized our current situation nicely. Now what is your decision, I shall not wait all night for you to decide something so simple. Yes or no?" He did not like having to take such a tone with his mate, but at times like this it was necessary. Dean could at times be too stubborn for his own good.

"Yes."

He felt joy and triumph spreading throughout his body and grace, he had won and Dean was one step closer to being his.

Dean sat on the edge of his bed in his empty room waiting for his brother to return trying and failing again and again to understand what just happened. Before he left Castiel had told him that their first date would take place the next night, and to be ready.

Even now two hours later he didn't know if he would ever be ready for something like this. He'd already given so much for his little brother and no matter what he did it always seemed like he was just giving more and more.

Shaking his head to clear his mind of such thoughts he waited for Sammy to come back so they could talk about what happens next. He had a feeling that these deals weren't exactly slanted in his favor and that in the end even if he won he would still lose.


	4. You're the Music in Me

**Summary for the Chapter:**

> Dean and Cas go on their first date, but while Dean's away Sam gets an unexpected surprise visitor.

[](http://s1063.photobucket.com/user/kasey19391/media/Chapter%20art/Deal%20me%20in/Chapter%204.jpg.html)

  
  


Dean stood alone in his hotel room waiting for the demon to arrive. The talk with Sammy had gone about as well as could be expected, he’d spent all of the night before and the day that followed it being told just how stupid he was. Joy.

Now he had to go on a date with a demon! It would be funny, if it wasn’t so totally just, not funny. What did a demon even think of when planning a date? Virgin sacrifice? Mass slaughter? Bowling?

If it was something so horrifying, so completely across the line, what would objecting do? Would that null the deal and forfeit Sammy’s life? If it did, would he still speak up? The date hadn’t even started yet and he was already fighting off a major brain twister of a headache. Son of a bitch!

“Are you ready to go Dean?” Whipping around to look at the demon behind him he nearly bit clean through his tongue to keep from crying out. He hated it when things snuck up on him.

“Yeah sure, hope I’m dressed alright, I mean it’s not like you told me what we’re doing anyway.” He hoped he would take the hint and give him a clue. No such luck, the bastard just tilted his head to the side and looked him up and down like he was really assessing his clothes. Like he would actually change if it didn’t pass scrutiny. Screw that!

“You are fine, let’s go Dean, we don’t want to be late.” He had a moment to wonder what the fuck he was reaching towards his face for, then the world went wonky. Oh God!

When he finally got his breathing and nausea under control he looked up to give him a piece of his mind for what the fuck he just did, whatever it was, and came face to face with his date location. Son of a bitch!

He just stared at the sign unable to comprehend. He could read the words but they made no sense at all. Of all the scenarios that passed through his mind for what the guy could pick, this hadn’t even being a passing idea.

**Rock and Roll hall of Fame and Museum, Cleveland Ohio.**

He’d always wanted to come here, and now he would be seeing it for the first time with a demon. Son of a bitch!

Bobby pulled the phone away from his ear and stared at it for a moment like that would somehow change the conversation he’d just had. 

Dean did what? 

That idjit. 

Hearing his name being shouted from far away he put the receiver back to his ear and sighed in resignation. This was really happening.

“Calm down Sam and just run through it once more.” The second telling did absolutely nothing to change the story at all.

He was still trying to form some kind of reply, figure out what the hell kind of question to ask first, when something changed.

In the background on Sam’s end he could hear another voice, at first he thought it was just the t.v., but then Sam paused and he figured that maybe Dean was back from his “date” already.

“Ruby?” Then the line went dead. 

Ruby! Wasn’t that the name of that demon broad? Trying to call the number back did him no good, and he couldn’t call Dean right now, who knew how the demon would react to being interrupted or even what the two of them were up to right then.

Best to just keep trying to reach Sam, and if nothing came of it soon he would just head down to help him himself. Hell maybe he should do that anyhow, it sounded like both boys were getting in over their heads. Gathering up his books he decided he could research the deal just as much on the road, and his boys needed him.

Hell, what they needed was a good swift kick in the keester, and that he could provide.

Castiel watched Dean as he rushed from one exhibit to the next. His beloved had been reticent at first, unwilling to enjoy himself, but then the different displays had begun to call to him. This was why he had chosen this particular place as their first date. His loves admiration of such things was very much a part of him and he had hoped that the venue would overpower any resentment he felt towards him personally.

It hurt to think that his mate felt such animosity towards him, but it was understandable and something he would gladly endure for the time being. He had already won after all, the end of this game was already decided, and he could afford to be patient and understanding for now.

“Dean please a small indulgence. Tell me, which are your favorite songs by each of these singers?” He already knew so much about him, but he wanted to know so much more. He wanted to see his emerald eyes spark with emotion and life as he spoke with him of something he cared for.

“They aren’t just singers, they are legends, that’s why they’re here.” The look of pure disgruntled affront on his future lovers face at the idea that these men would be nothing more than singers was amusing to say the least. He appeared to be genuinely offended on their behalf.

“Of course, forgive me, what are your favorite songs by these legends?” If he needed to breathe he imagined he would be holding his breath now as he waited to see if he would answer. If he chose not to he supposed he could insist, but that might not be the best way to gain what he desired in this particular instance. What to do?

Dean thought about just ignoring him and continuing to trying to enjoy this place like he was here on his own. Then again, if he pissed this thing off too much he might just decide to teach him a lesson in manners by going on a little murder spree right here. The place wasn’t crowded at the moment but there were more than enough people around to make him queasy at the thought of them being in the line of fire.

He hadn’t seen this guy go all bloodthirsty before, but it wasn’t like it was out of the realm for it to happen, there was no such thing as a good demon after all. Seeing no harm in answering the guy, he took a deep breath and began.

Looking to the left he saw Bruce Springsteen's hotel keys, oh if the walls of that hotel room could talk they would probably make anyone within ear shot blush.

“Well Bruce Springsteen has a lot of really classic stuff but if I had to pick a favorite I would have to go with Born in the U.S.A. I know that’s a little predictable, but there’s a reason it’s so popular. Plus that thing with Regan was just hilarious, most guys would have been flattered to have their song used in a presidential anything, but Bruce totally nailed them for using his shit without asking first. Classic.”

Looking down a little he saw the schoolboy outfit worn by Angus Young the guitarist of AC/DC. The mannequin didn’t do it justice, that thing was all kinds of weird, but at the same time it had its own special kind of style. No one else in the world could probably pull it off, but that just made it one of a kind.

“Most people love the 1979 album from AC/DC Highway to Hell, their first to sell over a million copies. Or they like Dirty Deeds Done Dirt Cheap which was originally released in 1976 but didn’t make it to the U.S. until 1981. Those are the ones that everyone knows from like movies and stuff, the ones used the most in commercials or referenced everywhere. They’re alright but I prefer You Shook Me All Night Long. Again kind of predictable, but come on, that one is amazing. I can’t tell you how many times I got laid to that thing in high school alone.”

Seeing a giant poster of Steven Tyler and Joey Kramer he couldn’t hold back a smile. Most people didn’t know how much he dug Aerosmith. He would shoot himself with the colt before he ever sat through one of their sappy power ballads, but they had some choice tunes.

“Steven Tyler has some killer vocals, he can reach a pitch that just makes you want to listen even more closely than you already are. Don’t get me wrong the dude has cranked out some sappy chick songs over the years, but he’s also got some really solid numbers mixed in with them. I have to say my go to for them, hands down has to be, Dream On.”

Seeing the whole section devoted to Black Sabbath he almost crossed himself, he wasn’t much for religion, but if he were this would be his church. He’d grown up listening to these dudes rock out, they were the soundtrack of his life.

“Black Sabbath no way, you know most in the business credited these guys with creating heavy metal. They were originally named Earth Blues Company or Earth, but they eventually changed it to what everyone now knows them as. This is where Ozzy Osbourne got his start. These guys were epic, true metal heads. Paranoid is like the best of them, pre Ozzy split.”

Castiel watched him light up as he spoke and he found himself smiling in return, even though he didn’t truly understand a word of what he spoke about. He had never heard any of these songs, but now that he knew which were his favorites he would be sure to rectify that mistake.

“Do you enjoy many bands such as these?” He watched him pause in his perusal of the many different displays, and for the first time he turned to look at him. He had been avoiding any form of contact with him, even eye contact until now. This music truly was a large part of his life to have such an effect on him.

“Oh yeah, Creedence Clearwater Revival, the Eagles, Guns N’ Roses, Metallica, Styx. All the hard core bands from the 70’s and 80’s.” He would have to be sure to research these hard core bands in great detail, if they meant so much to Dean he would learn all there was to know about them. He wondered what else meant so much to Dean? Maybe over the course of these dates he would find out.

Sam dropped the phone, hoping that Bobby would understand why he did it later, and reached for the closest weapon, a regular revolver, but it would have to do for now.

“Ruby? What the hell are you doing here?” The pert little blonde just looked at him like he was the dumbest creature she’d ever met that still had the power of speech. She was the demon that just barged into the room of a hunter, apparently un-armed so he supposed he could argue that one with her very convincingly.

“What happened Sam?” What the hell did she mean what happened? What happened when? And why wasn’t he just shooting her? Not that the gun would do much damage to her demonic hide, but it could at least give him the time he needed to find the colt, assuming Dean hadn’t taken it with him.

“What are you talking about?” At the very least he might be able to get some intel from her. If demons were going to be coming after them about something, then it would help if they knew more about what they wanted this time. Not that knowing would really do much beyond make them paranoid, or angry, but it would be better than not knowing.

“What the hell happened Sam? The underworld’s in a tizzy over something to do with your brother. What the hell happened to Dean?”


	5. Why Me

**Summary for the Chapter:**

> Dean and Castiel finish their date while Sam gets some company of his own...

[](http://s1063.photobucket.com/user/kasey19391/media/Chapter%20art/Deal%20me%20in/Chapter%205.jpg.html)

  
  


“What do you mean what happened to Dean? Dean's fine. Isn't he?” Did that demon do something to his brother? Why would Hell be in a snit about it if he had? This made no sense.

“That's kind of the problem Sam. Dean made a deal to save you, everyone's heard about it, but no one can find his contract or the crossroads demon that sealed the deal. So I'll ask you again, what the hell happened?”

Sam looked around the room like the answers he craved would suddenly appear out of thin air, but found nothing. Ruby had already come and gone, he’d told her he had no idea what she was talking about and hadn’t that gone over well, he didn’t want to risk telling her Castiel’s name until he had more information. He knew that Dean had definitely sold his soul, but then why was there no record? What the hell was going on?

Hearing a knock at the door he jumped up, only just now realizing that he’d been sat in the same spot for the past four hours without moving. His joints creaked and his muscles ached as he made his way across the small room to see who was visiting now. Opening the door he was almost relieved to find Bobby on the other side, if what Ruby said was true they were going to need all the help they could get.

“Bobby man, I’m glad you’re here. There’s so much we need to talk about.” He just hoped that Dean made it back in one piece so he could be a part of this little discussion as well. Stepping back to allow the closest thing he had to a father to pass through the threshold of his tiny little hotel room he tried to organize his thoughts. If he couldn’t explain this right, Bobby wouldn’t be able to help them at all.

“What the hell happened Sam, one second you’re yapping at me about a second deal your bone head brother made, then you’re yapping at Ruby of all people who just shows up here in your room, then I don’t hear a peep outta ya, so I race all the way over here to find you perfectly fine and in working order. What the hell happened Sam?”

Opening his mouth he meant to lay it all out for Bobby, to tell him about Ruby and Dean’s contract, about the second deal his brother was forced to make on his behalf. When no sound emerged from his open mouth he looked up into Bobby’s frustrated face and said the first thing that came to his mind.

“Dean’s still on his date.”

Dean tried to keep the scowl from his face, but from the looks he was getting he knew he wasn’t being all that successful. He was so confused, before this whole date thing started he’d been worried that Castiel would choose to do things that he would absolutely hate, things that would test his limits. Looking around at the people surrounding him his limits were being tested alright, just not the way he thought they would be.

He’d pictured murder and mayhem, not what would have been the perfect date if only he’d been on it with someone, hell anyone else. 

The night had begun at the Rock n’ Roll Hall of Fame in Cleveland, where he spent hours surrounded by the sounds of his childhood. Each new display bringing back memories that he’d forgotten long ago. Sitting up late at night with his dad in the impala waiting for whatever fugly they were after to show its face while he heard his favorite tunes for the first time. His dad’s fingers tapping along on the steering wheel.

If he closed his eyes he could practically smell the old leather and whiskey.

After they’d gone through every inch of the place, some parts twice, Castiel declared that he needed to be fed and that’s how they ended up here. He remembered this little roadside diner, his father had taken him and Sammy here for his twelfth birthday. It had been down the road from the hunt they’d been driving towards for two days straight, but still they stopped for a burger and a slice of pie. It was the one day a year when his dad would give his whole attention to his son, if only for the time it took to eat. 

It was the last birthday of his childhood, after that day his father decided he was finally old enough to be given more responsibilities. He was given a more active role in hunts, starting with the one they’d been driving towards when his birthday cropped up, he wasn’t just his brothers keeper anymore. This place was where a child died and a hunter was born.

Looking down at the meal set out before him, the same meal he’d eaten all those years ago, he began to get a sinking feeling in the pit of his stomach. He wasn’t completely sure what was causing it, but he knew it couldn’t be anything good. Even if the back of his mind, where his instincts lay wrestled into submission, was screaming at him that this was wrong, he did his best to push it all down as he shoved another bite of pie into his mouth. The food was just as good as he remembered it, but he could barely taste it. 

Finally he’d had enough, this thing had been staring at him probably not even blinking since this whole bizarre date began, he wanted answers damn it. He needed them, if he was going to keep his sanity through this whole social experiment from hell.

“Alright, what gives?” Throwing his napkin on the table he rested his fists on the table and leaned in close so their conversation wouldn’t be overheard. They were drawing enough attention as it was without having to worry about the nice men with the big nets coming to try and drag them both away to the loony bin. He had a mild brain freeze at the mental image that train of thought conjured for him in his mind, but he easily shook it off in favor of the answers that he demanded.

“Whatever do you mean Dean? You need to learn to be far more precise with your language, you leave a great deal to interpretation.” Even though his face never really changed, he could see the smirk hiding in his eyes. The little prick was enjoying this.

He was so overcome with his frustration at having his question dodged, that he let the answer he did receive wash over him, not really hear it at all.

“Fine you want precise, I’ll be specific. Why the hell are you doing this? You take over my deal, frying a demon in the process I might add. Then you show up out of nowhere to, as far as I can tell, sit in a chair and stare at me. Then you take the first opportunity you find to maneuver me into this new deal where you can basically go anywhere and do anything and what you do is what? Revisit my past? Drag up old memories of the good old days? So I’ll ask you one more time, what gives?” He just didn’t understand it, this demon was more powerful than any he’d come across in the past, but he wasn’t acting like a demon at all. 

Sure he was manipulative and opportunistic, but where was the murder? Where was the chaos? The mind games? Not that he was wishing for any of those things, but this whole lot of nothing wasn’t just confusing him, it was putting him on edge. He kept waiting for the other shoe to drop, and honestly he would prefer to pull the damn thing down himself than keep fucking waiting.

“Did you not enjoy our first date Dean?” Hoping that a little honesty would earn him a few answers he went with the truth over his usual bluster.

“I think you already know that I did. You took me to the one place I’ve been wanting to visit since it first opened back in ’95. Then you bring me here, the last place I ever remember my dad being just my dad, and give me the meal I ate when I was twelve years old. It’s like you decided to drag me down memory lane or something. The music of my childhood, followed by the food of it. What I can’t understand, and am hoping against hope you will clear up for me, is why? Why spare Sammy’s life, just to do this?” Spreading his arms out wide to encompass the whole diner he raised his brows to make sure the demon understood what this was. What the hell was the point? He knew there was one he just couldn’t seem to find it, too much forest to see any trees.

“Oh Dean, what would be the fun in explaining? I am sure that before our deal is done, you will have worked it out all on your own. You are incredibly intelligent Dean, more so than many give you credit for.” Clenching his fists he decided to ignore the compliment in lieu of something far more important, at least in his opinion. 

“Which deal?” This one or the one before? Was he implying that these dates would take a year to complete? It was possible, he’d been so worked up over Sammy and trying to keep Castiel from charging after him in a murderous rage he hadn’t even tried to place limits or time frames on this date deal.

Looking up he finally saw a smile spread across Castiels face and it sent a shiver down his spine. It was far too predatory to be even close to human.

“Good question, Dean.” Though it would seem it would be a question without an answer.

Castiel had just dropped Dean off with his loving brother and their mentor, determined to give his mate some space to process everything. He would go find something to do and leave Dean alone until morning at least, though he knew if he made it that long it would be a miracle. He supposed he could go to his brother and tell him all about his first date with Dean, Lucifer had always been supportive of him and all of his endeavors after all, and he would be interested to hear about his progress.

As he took flight, intending to allow his wings to carry him to his brothers’ side, he found himself in a deserted little park sitting on a bench thinking about his evening, alone. He thought again about going to his brother, but he found he did not wish to share the details of his courtship with anyone, even his blood kin. At least not yet. 

At the moment all he wanted to do was savor the memory of having Dean all to himself for the first time, as he sat silently surrounded by the quiet calm of night he replayed the events of the evening in his mind. Every expression, every syllable forever ingrained in his memory.

Watching Dean try to puzzle everything out, when he was still missing so many important pieces was a thing of beauty. Most of all he enjoyed watching his beloved come so close to understanding, to fall just shy of the mark. He knew that one day understanding would come to him, and with it a host of other thoughts and feelings would encroach on his mind, but until that day came Dean would continue to look to him for answers and understanding.

Looking up towards the night sky he let the smile he’d been keeping to himself spread across his face, life was beautiful. Everything was falling into place for him, for them, and the thought of it was enough to make him want to laugh, by this time next year he and Dean would be in hell, really getting to know one another. When that day finally came there would be nothing left between them, they would finally be one as they should have been all along.

How was that for a grand design.


End file.
